1. ORGANIC POLYMERS: THE SYNTHESIS OF NYLON
Experiment 25:
ORGANIC POLYMERS:
THE SYNTHESIS OF NYLON

2. Objectives:
To synthesize Nylon 6,10 from hexamethylene diamine and sebacoyl chloride.
To determine the length of the Nylon formed using a simple mathematical calculation.

3. SYNTHESIS OF AN AMIDE
Carboxylic Acid
amine
amide
Reacting a carboxylic acid with an amine yields an amide. Water is a by-product, and this reaction is slow without a catalyst.

4. SYNTHESIS OF AN AMIDE
amine
Acid chloride
amide
By using a carboxylic acid chloride, a more reactive carboxylic acid derivative, the rate of reaction can be increased. In this reaction, HCl is the by-product.

5. MECHANISM

6. Hexamethylene diamine
SYNTHESIS OF NYLON 6,10
Sebacoyl chloride
Hexamethylene diamine
In order to make a polyamide, such as Nylon 6,10, the amine molecule must have a –NH2 group at each end, and the acid chloride must have a –COCl group at each end.
The diamine and the diacid chloride bond together, end-on-end, to form very long chains.
Nylon 6,10 is made from hexamethylene diamine (the diamine) and sebacoyl chloride (the diacid chloride).

7. Hexamethylene diamine
SYNTHESIS OF NYLON 6,10
Hexamethylene diamine
Sebacoyl chloride

8. CLASSIFICATIONS OF SYNTHETIC POLYMERS
Synthetic polymers are classified by their method of synthesis.
Synthetic Method
Chain-growth
Step-growth
polystyrene
Polyamides (nylon)

9. NATURAL ORGANIC POLYMERS
Proteins
hair, skin, tissue
Polysaccharides
cellulose, starch
Polynucleotides
DNA, RNA

10. SYNTHETIC ORGANIC POLYMERS
Nylons
Polyesters
Acrylics
Polyvinyls
Plastic sheeting and plumbing materials
Polystyrenes
Insulating materials

11. EXPERIMENTAL PROCEDURE (Synthesis)
Pour diamine solution and diacid chloride in separate beakers.
Using forceps, grasp the film that forms at the interface of the two liquids.
Pull up slowly and wrap end of nylon string around a test tube.
Rotate the tube and count the number of revolutions made before no more nylon can be produced.

12. EXPERIMENTAL PROCEDURE (Analysis)
Calculate the length of the nylon string produced (in meters) using the following equation:
Nylon produced (m) =
(test tube diameter (m)) X (p) X (# test tube revolutions )

13. Test tube diameter (mm) # of test tube revolutions
Table 25.1
Test tube diameter (mm)
# of test tube revolutions
Length of nylon (m)

14. SAFETY CONCERNS CAUTION:
All chemicals are hazardous to the skin and eyes. Safety goggles and gloves are required during the experiment!!!

15. WASTE MANAGEMENT
Pour all waste from synthesis and solubility tests into container labeled
“ORGANIC WASTE (Polymers)”

16. CLEANING
Clean all glassware with soap, water, brush, and rinse with wash acetone before returning to lab drawer!
DO NOT return any glassware to lab drawer dirty or wet!

17. LABORATORY NOTEBOOK (Pre-lab)
OBJECTIVE (Must clearly state…)
What compounds will be made and how
What you will do with the compound once made
CHEMICAL EQUATION
Include the chemical equation middle of page 212.
TABLE OF PHYSICAL DATA (Complete the following table using MSDS sheets from or ONLY. Wikipedia is unacceptable.)
REFERENCE TO PROCEDURE (Must include…)
full title including edition and author names
page numbers where actual procedure can be found
Compound
MW (g/mol)
mp(oC)
bp(oC)
d (g/mL)
HAZARDS
Sebacoyl chloride X
Hexamethylene diamine
Sodium hydroxide
Hexane

18. LABORATORY NOTEBOOK (In-lab)
DATA/CALCULATIONS
Diameter of test tube
# revolutions
Length of nylon produced calculation
EXPERIMENTAL PROCEDURE
In paragraph form, BRIEFLY describe the procedure that you actually followed during the lab.
Paragraph must be written in PAST TENSE, PASSIVE VOICE.
Include any volumes or weights of chemicals used during the experiment.
Include any mistakes, accidents or observations if applicable.